Lasmiditan, known as COL-144 or LY573144, is a 5-HF1F receptor agonist. It is used to inhibit plasma protein extravasation, treat or prevent migraine and other diseases or symptoms related to dysfunction of 5-HF1F receptor. The chemical name is 2,4,6-trifluoro-N-[6-(1-methyl-piperidine-4-carbonyl)pyridin-2-yl]-benzamide. Its chemical structural is shown in formula (I) below:

Lasmiditan is a novel selective and efficient 5-HF1F receptor agonist. It increases activation of 5-HF1F receptor, while avoiding vasoconstrictive activity, inhibiting plasma protein extravasation, for treating or preventing migraine and other diseases or symptoms related to dysfunction of 5-HF1F receptor. Included among these disorders are migraine (including hemicephalic neuralgia, headache related to vascular diseases, neurovascular headache), general pain, trigeminal neuralgia, anxiety, panic disorder, depression, post-traumatic syndrome, dementia and other diseases.
Patent document CN100352817C disclosed lasmiditan, lasmiditan semi-succinate and hydrochloride and their preparation methods, meanwhile disclosed their characterization data of mass spectra, 1H-NMR, 13C-NMR, as well as melting points. According to the study of the present inventor, lasmiditan, obtained by the preparation method of embodiments 17 and 21 in CN100352817C, is a light brown oil-like amorphous form, which has the disadvantages including unstable solid form, susceptible to moisture absorption and poor morphology.
The embodiment 8 of patent document CN100352817C reported the preparation method of lasmiditan hydrochloride, in which it was mentioned that lasmiditan free base was oil-like. Lasmiditan hydrochloride obtained by the preparation method of embodiment 8 in CN100352817 is a white amorphous form, which has the disadvantages including unstable solid form, susceptible to moisture absorption and poor morphology.
The embodiment 2 of patent document U.S. Pat. No. 8,697,876B2, disclosed the preparation method of lasmiditan semi-succinate intermediates, including lasmiditan and lasmiditan hydrochloride. According to the study of the inventor, lasmiditan, prepared according to U.S. Pat. No. 8,697,876B2 is also a light brown oily amorphous form; and lasmiditan hydrochloride is also a white amorphous form.
In view of the defects in the prior art, it is still necessary to discover more new crystalline forms of lasmiditan in this field, with improved properties to meet the strict requirements of pharmaceutical preparations on the morphology, stability and other physicochemical properties of active substances.